7 things I wish I’d known before I started freelancing

Freelancers are revolutionizing the global workforce—but mostly in the afternoon, since you know how we like to sleep in.

Maybe you’re reading this article because you’re considering freelancing, but the fact is—ready or not—most everyone will be freelancing in 10 years. An Edelman Intelligence study revealed that the majority of the U.S. workforce will be freelance in 2027 if we continue at this current growth rate. The current statistics are surprising, too. As of this writing, 36% of U.S. workers are freelance, with Millennials leading the charge. Turns out that 47% of the generation makes their own hours.

Here are 7 truths about freelancing that I wish I’d known before I started.

Those who have never freelanced may have an idealized idea of the freelancer lifestyle: waking up past noon and going to work on your couch without pants on. There is some truth to that—sometimes I work without pants on, I’ll admit it!—but this narrow-minded thinking still leaves much of the reality of freelancing in the dark.

Unfortunately, you usually learn the most important lessons the hard way. I’ve been freelancing now for over ten years, first as a proofreader, then an editor and now as a writer. And I have to say, most of my success has been built upon the blunders, missteps and flat-out failures of my early years. And as a “welcome” to the new wave of freelancers, I’ve reflected on the 7 truths about freelancing that I wish I’d known before I started.

Take these tips to heart—put them on a post-it note! Tape them to your computer screen!—so you don’t make the same freelancing mistakes I did.

1. Create not one, but two, saving funds
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There’s a lot of rainy days in freelancing, so make sure your rainy-day fund can cover it. Via Pexels.

Traditionally, when a worker gets paid they set aside some money for spending cash and put the rest into a nest egg, which may be investments, a retirement fund or rainy day cash. That’s a smart plan, but won’t always work for freelancers who often face a unique financial concern called “Oh crap! My industry’s dryer than a bone this month!”

Freelancing is all about ebb and flow—sometimes there’s more work than you can handle, sometimes you couldn’t even pay people to hire you. Rule number one of freelancing is to work extra hard during the boon times so you have enough money for the hard times.

You always want to have enough savings to cover you for at least a month without work, just in case. Ideally, that would be in addition to any other savings you have for different purposes. The best way to achieve this is putting in extra hours when you can get them.

2. Stand up for yourself
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The business world can be a hard place—with clients sometimes taking advantage of those they hire. This is especially true for freelancers because we repeatedly do business with strangers. That’s why every freelancer needs to know how to stand up for him or herself.

When I first started freelancing, I’d give all my clients the benefit of the doubt. When they said I had to redo a project for free, I took it at face value. I just assumed they knew something I didn’t since they’d be working in the industry longer. But the more experience I raked in, the more I was able to recognize the thin line between labor and exploitation.

Don’t be afraid to stand up to clients if you feel you’re being treated unfairly. It’s likely that someone just made a honest mistake instead of trying to cheat you. And if the client isn’t reasonable and did try to cheat you intentionally, you want to stop working with them immediately anyway.

A good rule of thumb to avoid payment disagreements is to get everything in writing, even if just in an email.

3. Keep your eyes peeled for new clients
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Freelancers are always looking for new clients, even when they can’t possibly take on any new clients. As mentioned above, freelancing is an ebb and flow: a full schedule this month doesn’t guarantee a full schedule next month.

In my early freelancing years, I learned to set aside a couple hours every Sunday (outside of my normal working days) to submit to job posts. Not only did this leave me prepared for losing clients out of the blue, but it also gave me opportunities to choose clients I actually liked rather than whomever I could get.

Later on, you get better at recognizing new job opportunities, even when they’re not evident. It took me years to figure out I could just as easily make a new client at a bar as I could on an online job site.

Also, don’t forget the more work you produce, the more clients come to you, whether through referrals or people simply seeing your samples circulating around. At some point in your career, the snowball effects does most of the job hunting for you, but you still need to know how to address new client opportunities when they arise.

4. Set a fixed schedule
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As a human, you’re a creature of habit… use that to your advantage. Via Pexels.

If there’s one trait a freelancer needs to be successful, it’s discipline. No one’s going to tell you that you have to work, so you have to tell yourself to. The trouble is, the consequences aren’t immediate so it’s easy to give into temptation. If you skip a day or miss a deadline, you won’t feel the effects until weeks later when moths fly out of your wallet at the supermarket.

Most successful freelancers work on a fixed schedule: they get up at the same time every day and work the same hours every day. Luckily, you have the freedom of choosing what times work best for you.

The fantasy is that you can work “whenever you feel like it,” but the reality is, you usually won’t feel like working. Having a fixed schedule and the discipline to avoid the snooze button helps to establish a daily routine, which can save your paycheck from the days when you just don’t feel like getting out of bed.

5. Get the best accountant you can find
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Your first instinct may be to hate the person telling you how much Uncle Sam’s cut is, but don’t kill the messenger. The truth is, if you invest in a good accountant, it will pay for itself come tax time, maybe even with a little extra. This is doubly important for freelancers; as a one-person business, you are your entire Accounting department, so the more outside help you can find, the better.

Going in, I understood that things like my website hosting and phone bill could be deducted as business expenses, but there are so many more money-saving tactics that only a trained accountant would know. I didn’t realize just how much difference a good accountant makes until I switched and saw the difference in my refund. All I could think was how I wished I had switched years earlier.

6. Designate a workspace
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In other words, don’t work in bed. This is another aspect of the freelancer fantasy, where you think you can live a full and complete life without leaving the bed all day. It’s possible, and it works in theory, but in reality working and playing in the same location only meets with disaster. Almost every freelancer I know has a designated workspace that’s nothing else but a workspace.

Prosperous freelancers can afford an actual home office, but I know some young freelancers who work from a designated corner of their studio apartment. Personally, I try to avoid cabin fever altogether and work at coffee shops. I have a collection of 2 to 4 coffeeshops and alternate them daily so I don’t overstay my welcome at a single one.

7. Live with life on the chopping block
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It takes some getting used to, but you learn to live with it. Via Wikipedia.

Have you ever heard the fable “The Sword of Damocles”? In it, a king allows a peasant to feel like a king for a day: the peasant is given all the wealth and luxuries of a king, but the entire time there is a sword hanging over him from the ceiling, threatening to drop at any moment (a metaphor for the ever-present danger, in case it’s not obvious). That’s a lot like being a freelancer—except without the wealth and luxuries.

Whenever a company needs to tighten its belt, the freelancers are the first to go. While I’m lucky enough to have a couple “forever clients,” the vast majority are temporary. Don’t take it personally, though; it’s just part of the job. And often clients are just as sad to see you go as you are.

The important thing is that you’re not caught off-guard. This is one of the main reasons to have a reliable nest egg (#1) and to regularly look for clients (#3).

Takeaway: freelancing isn’t easy, but at least it’s fun
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What’s the biggest obstacle to freelancing? Most newcomers who are entertaining the idea of freelancing are thinking only about waking up late and working in their PJs, but to survive—and thrive—they’ll have to pay attention to the other side of things, like all the extra hours spent looking for new work or waiting months to get paid because of a lazy client. They focus only on the good because they don’t yet know of the bad. Freelancing presents a lot of freedoms and flexibility that salary-workers can only dream of, but those perks come with a cost.

Before you become a freelancer, have a realistic idea of what to expect. It’s still a job, with the same amount of work (if not more) than a salary job. It all depends on how you handle the lifestyle: freelancing can be either a never-ending struggle or everything you ever wanted.

Do you have any questions about freelancing that weren’t answered above? Ask me anything in the comments and I’ll answer to the best of my knowledge!

The author

Matt Ellis is a freelance content writer, specializing in web design and ecommerce. For over a decade he's been sharing his industry knowledge through ebooks, website copy, and blog articles just like this one. You can learn more about his career and writing services at https://www.mattelliscontentwriter.com/.

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Morgan Thomson

Mar 12 2018

I just wanted to alert you to a mistake in your article.
“Most newcomers who are entertaining the idea of freelancing are thinking only about waking up late and working in their PJs, but to survive—and thrive—they’lll have to pay attention to the other side of things, like all the extra hours spent looking for new work or waiting months to get paid because of a lazy client.”
In this sentence, taken from the section “Takeaway: freelancing isn’t easy, but at least it’s fun. In the third line, there is an extra “l” on they’ll.
Just thought I would let you know.

Hello!
I just found your site with this very article; quite helpful! I must admit that I am at a bit of a loss as to how to set up a safe and sound financial system for getting paid. I have never freelanced and want to start off on the right foot.
Any tips on what is the right way to set this up and what are some red flags for potentially sketchy gigs?
Thanks for sharing your knowledge and time!
-Best, Thomas

Hi Thomas,
I’m glad you liked the article! If you’re talking about actual financial software, PayPal is a good place to start. It’s secure, convenient, has a built-in invoicing system and most employers of freelancers already use it. There are transaction fees, though, but they’re under 5%.
About how to avoid getting scammed, I’m afraid that’s a bit trickier. I like to research prospective clients for a few minutes before committing: check their websites (and emails) for typos, check customer reviews for egregious complaints, check your contact’s LinkedIn, maybe do a generic Google search to reveal any bad press. If I’m still unsure, I’ll wait for payment on a first assignment before starting a second.
But I don’t want to scare you — in all my time doing this, I’ve only encountered a handful of people who consciously tried to cheat me. Once you get a few assignments under your belt, you’ll feel a lot more confident about choosing whom to work for.
I hope that helps!!

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